Transition metal-catalyzed asymmetric allylation

Topics in Organometallic Chemistry

Volumn 36, Issue , 2011, Pages 247-285

  Ding, Chang Hua ^a   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allylation; Asymmetric catalysis; Chiral ligand; Transition metal

Indexed keywords

EID: 80051693279     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-3-642-19472-6_8     Document Type: Article

References (166)

1. Trost BM, Crawley ML (2003) Chem Rev 103:2921
2. Lu Z, Ma S (2008) Angew Chem Int Ed 47:258
3. Denmark SE, Fu J (2003) Chem Rev 103:2763
4. Yamamoto H, Wadamoto M (2007) Chem Asian J 2:692
5. Shibasaki M, Kanai M (2008) Chem Rev 108:2853
6. Zhu J, Lu X (1987) J Chem Soc Chem Commun:1318
7. Huang YJ, Lu XY (1988) Acta Chim Sin 46:1113
8. Huang YJ, Lu XY (1988) Tetrahedron Lett 29:5663
9. Huang YJ, Lu XY (1986) Tetrahedron Lett 27:1615
10. Zhu J, Lu X (1986) Synthesis:563
11. Lu X, Zhu J, Huang J, Tao X (1987) J Mol Catal 41:235
12. Zhu J, Lu X (1987) Tetrahedron Lett 28:1897
13. Lu XY, Huang YJ (1984) J Organomet Chem 268:185
14. Lu XY, Huang YJ (1984) Acta Chim Sin 42:835
15. Lu XY, Lu L, Sun JH (1987) J Mol Catal 41:245
16. Lu XY, Zhu JY (1987) Acta Chim Sin 45:312
17. Lu XY, Tao X, Zhu J, Sun X, Xu J (1989) Synthesis:848
18. Xu Y, Zhou B (1987) J Org Chem 52:975
19. Zhou B, Xu Y (1988) J Org Chem 53:4419
20. You SL, Zhou YG, Hou XL, Dai LX (1998) Chem Commun:2765
21. Hayashi T, Togni A (1995) Ferrocenes. VCH, Weinheim, Germany
22. Togni A, Haltermann RL (1998) Metallocenes. VCH, Weinheim, Germany
23. Hayashi T, Konishi M, Fukushima M, Mise T, Kagotani M, Tajika M, Kumada M (1982) J Am Chem Soc 104:180
24. Richards CJ, Hibbs DE, Hurthouse MB (1995) Tetrahedron Lett 36:3745
25. Kuwano R, Uemura T, Saitoh M, Ito Y (1999) Tetrahedron Lett 40:1327
26. Bolm C, Fernandez KM, Seger A, Raabe G, Gunther K (1998) J Org Chem 63:7860
27. Fu GC (2000) Acc Chem Res 33:412
28. Pastor SD, Togni A (1989) J Am Chem Soc 111:2333
29. Togni A, Pastor SD (1990) J Org Chem 55:1649
30. Wally H, Widhalm M, Weissensteiner W, Schlögl KA (1993) Tetrahedron: Asymmetry 4:285
31. You SL, Hou XL, Dai LX, Yu YH, Xia W (2002) J Org Chem 67:4684
32. Liu D, Xie F, Zhang W (2007) Tetrahedron Lett 48:585
33. Zhang W, Yoneda Y, Kida T, Nakatsuji Y, Ikeda I (1998) Tetrahedron: Asymmetry 9:3371
34. Deng WP, Hou XL, Dai LX, Yu YH, Xia W (2000) Chem Commun:285
35. Deng WP, You SL, Hou XL, Dai LX, Yu YH, Xia W, Sun J (2001) J Am Chem Soc 123:6508
36. Tu T, Hou XL, Dai LX (2004) J Organomet Chem 689:3847
37. Pidcock A, Richards RE, Venanzi LM (1966) J Chem Soc A 1707
38. Venanzi LM (1968) Chem Br:162
39. Appleton TG, Clark HC, Manzer LE (1973) Coord Chem Rev 10: 335
40. Basolo F, Pearson RG (1962) Prog Inorg Chem 4:381
41. Tu T, Zhou YG, Hou XL, Dai LX, Dong XC, Yu YH, Sun J (2003) Organometallics 22:1255
42. Hu X, Dai H, Hu X, Chen H, Wang J, Bai C, Zheng Z (2002) Tetrahedron: Asymmetry 13:1687
43. Hu X, Chen H, Hu X, Dai H, Bai C, Wang J, Zheng Z (2002) Tetrahedron Lett 43:9179
44. Hu X, Chen H, Dai H, Hu X, Zheng Z (2003) Tetrahedron: Asymmetry 14:2073
45. Hu X, Chen H, Dai H, Zheng Z (2003) Tetrahedron: Asymmetry 14:3415
46. Hu X, Dai H, Bai C, Chen H, Zheng Z (2004) Tetrahedron: Asymmetry 15:1065
47. Hu X, Chen H, Zheng Z (2005) Adv Synth Catal 347:541
48. Huang JD, Hu XP, Yu SB, Deng J, Wang DY, Duan ZC, Zheng Z (2007) J Mol Catal A: Chem 270:127
49. Huang JD, Hu XP, Zheng Z (2008) Chin Chem Lett 19:261
50. Hu XP, Chen HL, Dai HC, Hu XQ, Zheng Z (2003) Chin Chem Lett 14:1113
51. Lam FL, Au-Yeung TTL, Cheung HY, Kok SHL, Lam WS, Wong KY, Chan ASC (2006) Tetrahedron: Asymmetry 17:497
52. Cheung HY, Yu WY, Au-Yeung TTL, Zhou Z, Chan ASC (2009) Adv Synth Catal 351:1412
53. Niu JL, Wang MC, Kong PP, Chen QT, Zhu Y, Song MP (2009) Tetrahedron 65:8869
54. Chen X, Guo R, Li Y, Chen G, Yeung CH, Chan ASC (2004) Tetrahedron: Asymmetry 15:213
55. Hou XL, Wu XW, Dai LX, Cao BX, Sun J (2000) Chem Commun:1195
56. Allen JV, Goote SJ, Dawson GJ, Frost CG, Martin CJ, Williams JMJ (1994) J Chem Soc Perkin Trans 1 15:2065
57. Wu H, Wu XW, Hou XL, Dai LX, Wang QR (2002) Chin J Chem 20:816
58. Hou XL, Dong DX, Yuan K (2004) Tetrahedron: Asymmetry 15:2189
59. Wu XW, Yuan K, Sun W, Zhang MJ, Hou XL (2003) Tetrahedron: Asymmetry 14:107
60. Jiang B, Lei Y, Zhao XL (2008) J Org Chem 73:7833
61. Zhang A, Feng Y, Jiang B (2000) Tetrahedron: Asymmetry 11:3123
62. Jiang B, Huang ZG (2007) Tetrahedron Lett 48:1703
63. Jiang B, Huang ZG, Cheng KJ (2006) Tetrahedron: Asymmetry 17:942
64. Gong L, Chen G, Mi A, Jiang Y, Fu F, Cui X, Chan ASC (2000) Tetrahedron: Asymmetry 11:4297
65. Chen G, Li X, Zhang H, Gong L, Mi A, Cui X, Jiang Y, Choi MCK, Chan ASC (2002) Tetrahedron: Asymmetry 13:809
66. Wang QF, He W, Liu XY, Chen H, Qin XY, Zhang SY (2008) Tetrahedron: Asymmetry 19:2447
67. Wang Y, Li X, Ding K (2002) Tetrahedron: Asymmetry 13:1291
68. Wang Y, Guo H, Ding K (2000) Tetrahedron: Asymmetry 11:4153
69. Wang Y, Li X, Sun J, Ding K (2003) Organometallics 22:1856
70. Zhang R, Yu L, Xu L, Wang Z, Ding K (2001) Tetrahedron Lett 42:7659
71. Zhao D, Ding K (2003) Org Lett 5:1349
72. Zhao D, Sun J, Ding K (2004) Chem Eur J 10:5952
73. Jiang ZD, Meng ZH (2007) Chin J Chem 25:542
74. Zhang W, Xie F, Yoshinaga H, Kida T, Nakatsuji Y, Ikeda I (2006) Synlett:1185
75. Tian F, Yao D, Zhang YJ, Zhang W (2009) Tetrahedron 65:9609
76. Wang F, Zhang YJ, Wei H, Zhang J, Zhang W (2007) Tetrahedron Lett 48:4083
77. Wei H, Zhang YJ, Wang F, Zhang W (2008) Tetrahedron: Asymmetry 19:482
78. Zhang YJ, Wei H, Zhang W (2009) Tetrahedron 65:1281
79. Li XG, Cheng X, Ma JA, Zhou QL (2001) J Organomet Chem 640:65
80. Li ZP, Tang FY, Xu HD, Wu XY, Zhou QL, Chan ASC (2003) J Mole Catal A: Chem 193:89
81. Davies IW, Gerena L, Castonguay L, Senanayake CH, Larsen RD, Verhoeven TR, Reider PJ, (1996) Chem Commun:753
82. Davies IW, Deeth RJ, Larsen RD, Reider PJ (1999) Tetrehedron Lett 40:1233
83. Denmark SE, Stiff CM (2000) J Org Chem 65:5875
84. Xie JH, Zhou QL (2008) Acc Chem Res 41:581
85. Xie JH, Duan HF, Fan BM, Cheng X, Wang LX, Zhou QL (2004) Adv Synth Catal 346:625
86. Dai WM, Yeung KKY, Liu JT, Zhang Y, Williams ID (2002) Org Lett 4:1615
87. Dai WM, Yeung KKY, Leung WH, Haynes RK (2003) Tetrahedron: Asymmetry 14:2821
88. Liu QB, Zhou YG (2007) Tetrahedron Lett 48:2101
89. Meng X, Li X, Xu D (2009) Tetrahedron: Asymmetry 20:1402
90. Fu B, Du DM, Xia Q (2004) Synthesis:221
91. Zhang W, Xu Q, Shi M (2004) Tetrahedron: Asymmetry 15:3161
92. Zhang W, Xu Q, Shi M (2004) Tetrahedron: Asymmetry 15:3467
93. Li SJ, Zhong JH, Wang YG (2006) Tetrahedron: Asymmetry 17:1650
94. Gao Y, Li X, Chen W, Xu D (2008) Lett Org Chem 5:346
95. Chen J, Lang F, Li D, Cun L, Zhu J, Deng J, Liao J (2009) Tetrahedron: Asymmetry 20:1953
96. Kwong HL, Yeung HL, Lee WS, Wong WT (2006) Chem Commun 4841
97. You SL, Hou XL, Dai LX (2001) J Organomet Chem 762:637-639
98. Liu D, Xie F, Zhang W (2007) J Org Chem 72:6992
99. Xie F, Liu D, Zhang W (2008) Tetrahedron Lett 49:1012
100. Wang Y, Ding K (2001) J Org Chem 66:3238
101. Cheung HY, Yu WY, Lam FL, Au-Yeung TTL, Zhou Z, Chan TH, Chan ASC (2007) Org Lett 9:4295
102. Hiroi K, Abe J, Suya K, Sato S, Koyama T (1994) J Org Chem 59:203
103. Ibrahem I, Córdova A (2006) Angew Chem Int Ed 45:1952
104. Weix DJ, Hartwig JF (2007) J Am Chem Soc 129:7720
105. Liu D, Xie F, Zhang W (2007) Tetrahedron Lett 48:7591
106. Zhao X, Liu D, Xie F, Zhang W (2009) Tetrahedron 65:512
107. Lam FL, Au-Yeung TTL, Kwong FY, Zhou Z, Wong KY, Chan ASC (2008) Angew Chem Int Ed 47:1280
108. Trost BM, Schroeder GM (1999) J Am Chem Soc 121:6759
109. You SL, Hou XL, Dai LX, Zhu XZ (2001) Org Lett 3:149
110. Yan XX, Liang CG, Zhang Y, Hong W, Cao BX, Dai LX, Hou XL (2005) Angew Chem Int Ed 44:6544
111. Zhang K, Peng Q, Hou XL, Wu YD (2008) Angew Chem Int Ed 47:1741
112. Nakoji M, Kanayama T, Okino T, Takemoto Y (2002) J Org Chem 67:7418
113. Kanayama T, Yoshida K, Miyabe H, Kimachi T, Takemoto Y (2003) J Org Chem 68:6197
114. Buldwin IC, Williams JMJ, Beckett RP (1995) Tetrahedron: Asymmetry 6:515
115. You SL, Hou XL, Dai LX, Cao BX, Sun J (2000) Chem Commun:1933
116. Hu X, Bai C, Dai H, Chen H, Zheng Z (2004) J Mol Catal A: Chem 218:107
117. You SL, Luo YM, Deng WP, Hou XL, Dai LX (2001) J Organomet Chem 845:637-639
118. Hayashi T, Kawatsura M, Uozumi Y (1998) J Am Chem Soc 120:1681
119. Prétôt R, Pfaltz A (1998) Angew Chem Int Ed 37:323
120. Pamies O, Dieguez M, Claver C (2005) J Am Chem Soc 127:3646
121. Faller JW, Wilt JC (2005) Organometallics 24:5076
122. Hilgraf R, Pfaltz A (2005) Adv Synth Catal 347:61
123. You SL, Zhu XZ, Luo YM, Hou XL, Dai LX (2001) J Am Chem Soc 123:7471
124. Corey EJ, Guzman-Perez A (1998) Angew Chem Int Ed 37:388
125. Christoffers J, Mann A (2001) Angew Chem Int Ed 40:4591
126. Hou XL, Sun N (2004) Org Lett 6:4399
127. Trost BM, Hildbrand S, Dogra K (1999) J Am Chem Soc 121:10416
128. Takeuchi R, Tanabe K (2000) Angew Chem Int Ed 39:1975
129. Lipowsky G, Helmchen G (2004) Chem Commun:116
130. Lipowski G, Miller N, Helmchen G (2004) Angew Chem Int Ed 43:4595
131. Zheng WH, Sun N, Hou XL (2005) Org Lett 7:5151
132. Zheng WH, Zheng BH, Zhang Y, Hou XL (2007) J Am Chem Soc 129:7718
133. Chen G, Deng Y, Gong L, Mi A, Cui X, Jiang Y, Choi MCK, Chan ASC (2001) Tetrahedron: Asymmetry 12:1567
134. Aramaki Y, Chiba K, Tada M (1995) Phytochemistry 38:1419
135. Crockett SL, Schuhly W, Belaj F, Khan IA (2004) Acta Crystallogr Sect E 60:2174
136. Tanaka N, Okasaka M, Ishimaru Y, Takaishi Y, Sato M, Okamoto M, Oshikawa T, Ahmed SU, Consentino LM, Lee KH (2005) Org Lett 7:2997
137. Trost BM, Jiang CH (2001) J Am Chem Soc 123:12907
138. Trost BM, Sacchi KL, Schroeder GM, Asakawa N (2002) Org Lett 4:3427
139. Trost BM, Dogra K, Franzini M (2004) J Am Chem Soc 126:1944
140. Du C, Li L, Li Y, Xie Z (2009) Angew Chem Int Ed 48:7853
141. Yorimitsu H, Oshima K (2005) Angew Chem Int Ed 44:4435
142. He H, Zheng XJ, Li Y, Dai LX, You SL (2007) Org Lett 9:4339
143. Tunge JA, Burger EC (2005) Eur J Org Chem 9:1715
144. You SL, Dai LX (2006) Angew Chem Int Ed 45:5246
145. Mohrand JT, Stoltz BM (2007) Chem Asian J 2:1476
146. Liu WB, He H, Dai LX, You SL (2008) Org Lett 10:1815
147. Liu WB, He H, Dai LX, You SL (2009) Synthesis:2076
148. Liu WB, Zheng SC, He H, Zhao XM, Dai LX, You SL (2009) Chem Commun:6604
149. He H, Liu WB, Dai LX, You SL (2009) J Am Chem Soc 131:8346
150. He H, Liu WB, Dai LX, You SL (2010) Angew Chem Int Ed 49:1496
151. Shi WJ, Wang LX, Fu Y, Zhu SF, Zhou QL (2003) Tetrahedron: Asymmetry 14:3867
152. Dong L, Xu YJ, Cun LF, Cui X, Mi AQ, Jiang YZ, Gong LZ (2005) Org Lett 7:4285
153. He XC, Wang B, Bai D (1998) Tetrahedron Lett 39:411
154. He XC, Wang B, Yu G, Bai D (2001) Tetrahedron: Asymmetry 12:3213
155. Zhao D, Wang Z, Ding K (2005) Synlett:2067
156. Shu W, Yang Q, Jia G, Ma S (2008) Tetrahedron 64:11159
157. Shu W, Ma S (2009) Chem Commun:6198
158. Shu W, Yang Q, Ma S (2009) Adv Synth Catal 351:2807
159. Shi M, Lei GX, Masaki Y (1999) Tetrahedron: Asymmetry 10:2071
160. Shi M, Sui WS (2000) Tetrahedron: Asymmetry 11:773
161. Wang CJ, Shi M (2003) Eur J Org Chem:2823
162. Li X, Liu X, Fu Y, Wang L, Zhou L, Feng X (2008) Chem Eur J 14:4796
163. Zhu SF, Yang Y, Wang LX, Liu B, Zhou QL (2005) Org Lett 7:2333
164. Qiao XC, Zhu SF, Zhou QL (2009) Tetrahedron: Asymmetry 20:1254
165. Zhang TZ, Dai LX, Hou XL (2007) Tetrahedron: Asymmetry 18:251
166. Wang W, Zhang T, Shi M (2009) Organometallics 28:2640